CN1671769B - 聚乙二醇醛衍生物 - Google Patents
聚乙二醇醛衍生物 Download PDFInfo
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- CN1671769B CN1671769B CN038176491A CN03817649A CN1671769B CN 1671769 B CN1671769 B CN 1671769B CN 038176491 A CN038176491 A CN 038176491A CN 03817649 A CN03817649 A CN 03817649A CN 1671769 B CN1671769 B CN 1671769B
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- Prior art keywords
- compound
- oxygen
- formula
- halogen
- polyethylene glycol
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- 229920001223 polyethylene glycol Polymers 0.000 title claims abstract description 85
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- 239000002202 Polyethylene glycol Substances 0.000 title claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 238000000034 method Methods 0.000 claims abstract description 35
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- -1 methoxyl group Chemical group 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
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- 239000012964 benzotriazole Substances 0.000 claims description 6
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- 238000001727 in vivo Methods 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 229960001388 interferon-beta Drugs 0.000 description 1
- 229940047122 interleukins Drugs 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/324—Polymers modified by chemical after-treatment with inorganic compounds containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2615—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen the other compounds containing carboxylic acid, ester or anhydride groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
- C08G65/2621—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups
- C08G65/2624—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups containing aliphatic amine groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Polyethers (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39819602P | 2002-07-24 | 2002-07-24 | |
| US60/398,196 | 2002-07-24 | ||
| PCT/EP2003/007734 WO2004013205A1 (en) | 2002-07-24 | 2003-07-16 | Polyethylene glycol aldehyde derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1671769A CN1671769A (zh) | 2005-09-21 |
| CN1671769B true CN1671769B (zh) | 2010-05-12 |
Family
ID=31495721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN038176491A Expired - Fee Related CN1671769B (zh) | 2002-07-24 | 2003-07-16 | 聚乙二醇醛衍生物 |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US7273909B2 (de) |
| EP (1) | EP1539857B1 (de) |
| JP (1) | JP4071238B2 (de) |
| KR (1) | KR100615753B1 (de) |
| CN (1) | CN1671769B (de) |
| AR (1) | AR040607A1 (de) |
| AT (1) | ATE344289T1 (de) |
| AU (1) | AU2003250971B2 (de) |
| BR (1) | BR0312863B1 (de) |
| CA (1) | CA2493221C (de) |
| DE (1) | DE60309482T2 (de) |
| DK (1) | DK1539857T3 (de) |
| ES (1) | ES2274277T3 (de) |
| GT (1) | GT200300154A (de) |
| HR (1) | HRP20050026A2 (de) |
| IL (1) | IL165920A0 (de) |
| JO (1) | JO2400B1 (de) |
| MX (1) | MXPA05000799A (de) |
| NO (1) | NO336974B1 (de) |
| PA (1) | PA8577601A1 (de) |
| PE (1) | PE20040703A1 (de) |
| PL (1) | PL214871B1 (de) |
| PT (1) | PT1539857E (de) |
| RU (1) | RU2288212C2 (de) |
| TW (1) | TWI276647B (de) |
| UY (1) | UY27902A1 (de) |
| WO (1) | WO2004013205A1 (de) |
| ZA (1) | ZA200410296B (de) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA05002632A (es) | 2002-09-09 | 2005-09-20 | Nektar Therapeutics Al Corp | Metodo para preparar derivados de polimeros solubles en agua que portan un acido carboxilico terminal. |
| GEP20074193B (en) | 2002-09-09 | 2007-09-10 | Nektar Therapeutics Al Corp | Water-soluble polymer alkanals |
| US20050214250A1 (en) | 2003-11-06 | 2005-09-29 | Harris J M | Method of preparing carboxylic acid functionalized polymers |
| US7989554B2 (en) * | 2006-01-10 | 2011-08-02 | Enzon Pharmaceuticals, Inc. | Reacting polyalkylene oxide with base, tertiary alkyl haloacetate, then acid to prepare polyalkylene oxide carboxylic acid |
| US20090252703A1 (en) * | 2006-10-19 | 2009-10-08 | Gegg Jr Colin V | Use of alcohol co-solvents to improve pegylation reaction yields |
| WO2008048079A1 (en) * | 2006-10-20 | 2008-04-24 | Postech Academy-Industry Foundation | Long acting formulation of biopharmaceutical |
| US8247493B2 (en) * | 2007-10-22 | 2012-08-21 | Postech Academy-Industry Foundation | Long acting formulation of biopharmaceutical |
| KR100967833B1 (ko) * | 2008-05-20 | 2010-07-05 | 아이디비켐(주) | 고순도의 폴리에틸렌글리콜 알데하이드 유도체의 제조방법 |
| WO2010030366A2 (en) * | 2008-09-11 | 2010-03-18 | Nektar Therapeutics | Polymeric alpha-hydroxy aldehyde and ketone reagents and conjugation method |
| RU2439091C1 (ru) * | 2010-10-06 | 2012-01-10 | Общество С Ограниченной Ответственностью "Форт" (Ооо "Форт") | Производные полиэтиленгликоля, содержащие ароматическую диазогруппу |
| EP2592103A1 (de) | 2011-11-08 | 2013-05-15 | Adriacell S.p.A. | Polymeraldehydderivate |
| CN105377307B (zh) * | 2013-06-24 | 2019-09-24 | Abl生物公司 | 具有改进的稳定性的抗体-药物缀合物及其用途 |
| KR102247701B1 (ko) | 2016-02-26 | 2021-05-03 | 한미정밀화학주식회사 | 폴리에틸렌글리콜 디알데히드 유도체의 제조방법 |
| AR107823A1 (es) | 2016-03-07 | 2018-06-06 | Hanmi Pharm Ind Co Ltd | Derivados de polietilenglicol y uso de los mismos |
| JP7377195B2 (ja) * | 2017-09-29 | 2023-11-09 | ハンミ ファーマシューティカル カンパニー リミテッド | リンカーとして非ペプチド性重合体結合脂肪酸誘導体化合物を含むタンパク質結合体及びその製造方法 |
| AU2022409717A1 (en) | 2021-12-16 | 2024-05-30 | Pags Co., Ltd. | Cell penetrating polypeptides (cpps) and their use in human therapy |
| EP4480497A1 (de) | 2023-06-21 | 2024-12-25 | RDP Pharma AG | Biokonjugate für die onkologie |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5252714A (en) * | 1990-11-28 | 1993-10-12 | The University Of Alabama In Huntsville | Preparation and use of polyethylene glycol propionaldehyde |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5770577A (en) * | 1994-11-14 | 1998-06-23 | Amgen Inc. | BDNF and NT-3 polypeptides selectively linked to polyethylene glycol |
| CH690143A5 (de) * | 1995-01-27 | 2000-05-15 | Rieter Automotive Int Ag | Lambda/4-Schallabsorber. |
| US5672662A (en) * | 1995-07-07 | 1997-09-30 | Shearwater Polymers, Inc. | Poly(ethylene glycol) and related polymers monosubstituted with propionic or butanoic acids and functional derivatives thereof for biotechnical applications |
| US5990237A (en) * | 1997-05-21 | 1999-11-23 | Shearwater Polymers, Inc. | Poly(ethylene glycol) aldehyde hydrates and related polymers and applications in modifying amines |
| US6465694B1 (en) * | 1998-10-26 | 2002-10-15 | University Of Utah Research Foundation | Method for preparation of polyethylene glycol aldehyde derivatives |
| JO2291B1 (en) * | 1999-07-02 | 2005-09-12 | اف . هوفمان لاروش ايه جي | Erythropoietin derivatives |
| KR100488351B1 (ko) * | 2001-12-11 | 2005-05-11 | 선바이오(주) | 신규한 폴리에틸렌글리콜-프로피온알데히드 유도체 |
| AU2002357806A1 (en) | 2001-12-11 | 2003-06-23 | Sun Bio, Inc. | Novel monofunctional polyethylene glycol aldehydes |
-
2003
- 2003-07-16 EP EP03766194A patent/EP1539857B1/de not_active Expired - Lifetime
- 2003-07-16 CA CA002493221A patent/CA2493221C/en not_active Expired - Fee Related
- 2003-07-16 PL PL375266A patent/PL214871B1/pl unknown
- 2003-07-16 MX MXPA05000799A patent/MXPA05000799A/es active IP Right Grant
- 2003-07-16 CN CN038176491A patent/CN1671769B/zh not_active Expired - Fee Related
- 2003-07-16 JP JP2004525223A patent/JP4071238B2/ja not_active Expired - Fee Related
- 2003-07-16 PT PT03766194T patent/PT1539857E/pt unknown
- 2003-07-16 RU RU2005105568/04A patent/RU2288212C2/ru not_active IP Right Cessation
- 2003-07-16 DE DE60309482T patent/DE60309482T2/de not_active Expired - Lifetime
- 2003-07-16 DK DK03766194T patent/DK1539857T3/da active
- 2003-07-16 WO PCT/EP2003/007734 patent/WO2004013205A1/en active IP Right Grant
- 2003-07-16 AU AU2003250971A patent/AU2003250971B2/en not_active Ceased
- 2003-07-16 BR BRPI0312863-6A patent/BR0312863B1/pt not_active IP Right Cessation
- 2003-07-16 AT AT03766194T patent/ATE344289T1/de active
- 2003-07-16 ES ES03766194T patent/ES2274277T3/es not_active Expired - Lifetime
- 2003-07-16 HR HR20050026A patent/HRP20050026A2/hr not_active Application Discontinuation
- 2003-07-16 KR KR1020057001223A patent/KR100615753B1/ko not_active Expired - Fee Related
- 2003-07-20 JO JO200383A patent/JO2400B1/en active
- 2003-07-21 AR AR20030102609A patent/AR040607A1/es not_active Application Discontinuation
- 2003-07-21 PA PA20038577601A patent/PA8577601A1/es unknown
- 2003-07-21 PE PE2003000727A patent/PE20040703A1/es not_active Application Discontinuation
- 2003-07-21 TW TW092119827A patent/TWI276647B/zh not_active IP Right Cessation
- 2003-07-21 US US10/623,978 patent/US7273909B2/en not_active Expired - Fee Related
- 2003-07-22 UY UY27902A patent/UY27902A1/es not_active Application Discontinuation
- 2003-07-23 GT GT200300154A patent/GT200300154A/es unknown
-
2004
- 2004-12-21 ZA ZA200410296A patent/ZA200410296B/en unknown
- 2004-12-22 IL IL16592004A patent/IL165920A0/xx not_active IP Right Cessation
-
2005
- 2005-01-03 NO NO20050019A patent/NO336974B1/no not_active IP Right Cessation
-
2007
- 2007-03-14 US US11/724,009 patent/US20070167606A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5252714A (en) * | 1990-11-28 | 1993-10-12 | The University Of Alabama In Huntsville | Preparation and use of polyethylene glycol propionaldehyde |
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